Q1Key_Wi02 - NU, Winter2002 #6 b) ( 2 1. (12 pts) Complete...

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Unformatted text preview: NU, Winter2002 #6 b) ( 2 1. (12 pts) Complete each of the following reactions by providing the missing starting materials, reagent set(s), or product (only the carbon-containing major product is necessary). If a reaction does not occur, please state so. Your answers should be consistent with any stereochemistry the reaction may require. \A Q” g .. i z a 1)Hg(OAc)2,H20 Uri, / C0 ——-—-—- 03 JL/ \ x :.H."3%r\\\\ \ (EU a?” L’— 9: *3K ‘3" V . C /,(;../2.c;‘¢; L g} Ho 9' )7-(‘a/Jt): rim kf ‘3/7 \ 0') OH MOB ‘ o “agi‘z w( BC’OH— Qut‘ 05.0.3 vf( molt , 7 [04: .V /( 1 . "HOH /’7 [\lmN'fi; ‘Hfirfl‘ BOPK “'—" F5r *IZ. " "so-11 ‘4 I, 4 Z NU, Winter 2002 3 b. (9 pts) Propose a mechanism for the following reaction using the curved arrow formalism. Provide all proton transfer steps. 0;; dil. H30+ OH + . AOMe 2EtLI ——————> —-——-—-> W R? at La Eu ((3 0 H00“). all J;th k ._.._..> news . 5t 2%? /<_€j’ 9c Zw/E/ 3. a. (10 pts). Propose a synthesis of the following compound from methane (as the only starting material) using only the reactions that you learned thus far this academic year. You may use an 91‘ A necessary inorganic reagents. ( §MW#( ‘ Lw+flfla j" '2, 20¢ “a Whitley (tbs-j CL“ 3“?— 00 E0 FILM“; E thtan L) CUan an M, H; W” I ind-.90? 25:31: - = "H (3,15 ‘ (n W75 , Owns 13L N U, Winter 2002 4 b. (15 pts). Propose a synthesis of the following compound from cyclopentanone (as the only carbon- containing starting material) using only the reactions that you learned in Chem 210-]. You may used any necessary inorganic reagents, and mCPBA. Note that in the context of this problem, Grignard and alkylithium are not inorganic reagent, you will have to make them from the appro riate o inorganic fragments. a?“ 1H190+ 0W- 2": (+3» 9:: E§ ...
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Q1Key_Wi02 - NU, Winter2002 #6 b) ( 2 1. (12 pts) Complete...

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